7500-54-1

Upstream product

• 613-73-0 1,2-phenylenediacetonitrile 

Downstream Products

• 15299-53-3 3-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benz[d]azepine 
• 15987-50-5 1,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one 
• 7500-53-0 1,2-Phenylenediacetic acid 
• 87813-67-0 (2-carbamoylmethyl-phenyl)-acetic acid 
• 2184-00-1 2,4-Dioxo-2,3,4,5-tetrahydro-1H-3-benzazepin 

Relevant academic research and scientific papers

Transfer Hydration of Dinitriles to Dicarboxamides

We present a robust method for double transfer hydration of dinitriles to afford diamides. The transfer hydration of 1, n -dinitriles (n = 1-6) proceeds smoothly in the presence of a palladium(II) catalyst with acetamide as a water donor, affording the corresponding diamides in moderate to high yields, without involving significant side reactions such as monohydration or cyclization. The equilibrium was shifted in the forward direction by removing coproduced acetonitrile under reduced pressure.

Regioselective biotransformations of dinitriles using Rhodococcus sp. AJ270

A variety of dinitriles have been hydrolysed selectively under very mild conditions using Rhodococcus sp. AJ270. Aliphatic dinitriles NC[CH2]nCN 1 undergo regioselective hydrolysis to give the mono acids 2 with up to 4 methylenes between the nitrile functions while those with n > 4 give the diacids 3 in good yield. Dinitriles NC[CH2]nX[CH2]nCN 4 bearing an ether or sulfide linkage are efficiently transformed into the mono acids 5 when an oxygen is placed β, γ or δ to the cyano group or a β- or γ-sulfur is present. Hydrolysis of N,N-bis(2-cyanoethyl)anilines 4h-j takes place slowly affording exclusively the monoacids 5h-j while the monocyano amides 5o-p are obtained as the sole isolable product from rapid hydrolysis of the corresponding N,N-bis(2-cyanomethyl)butylamine 4o and N,N-bis(3-cyanopropyl)butylamine 4p. Higher homologues of arylimino- and butylimino-dinitriles are inert to enzymatic hydrolysis. A variety of other aliphatic dinitriles have been converted readily into mono acids in good to excellent yields except for o-phenylenediacetonitrile which gives o-phenylenediacetamide as the major product. The title organism also effects the hydrolysis of aromatic dinitriles with regiocontrol such as m- and p-dicyanobenzenes, but nct the ortho-substituted analogue. The scope and limitations of this enzymatic process have been systematically studied and the mechanism of regioselective hydrolysis has been discussed in terms of a chelation-deactivation effect.

Rationalisation of the regioselective hydrolysis of aliphatic dinitriles with Rhodococcus rhodochrous AJ270

Aliphatic dinitriles undergo regioselective hydrolysis with the title organism to give monoacids with up to four methylenes between the nitrile functions (optimally 2-3) or when either an oxygen is placed β, γ or δ to the nitrile (δ-placement being optimal) or β or γ (optimally γ) but not δ sulfur substituents are present; nitrogen substituents appear to behave as for oxygen but suffer a steric limitation of the size of the nitrogen substituent.